Senior Delivery Manager

At Robots & Pencils, we drive digital innovation by building meaningful, scalable software products for forward-thinking clients. We are seeking an experienced and strategic Senior Delivery Manager to lead complex, enterprise-grade programs involving AI-enabled automation, cloud-native platforms, and mobile-first experiences.

This role will lead distributed teams across North America and Eastern Europe and is responsible for aligning delivery execution with client expectations, regulatory constraints, and long-term business outcomes. You will play a critical role in high-impact engagements within highly regulated environments, including utilities and government-adjacent organizations.

This position includes monthly travel to client sites in the U.S. to support relationship building, delivery alignment, and strategic planning.

Key Responsibilities

Team Leadership & Coordination

• Lead high-performing, distributed delivery teams across backend, mobile, web, data, and AI disciplines, fostering accountability, collaboration, and delivery excellence.

• Act as the operational bridge between onshore stakeholders and offshore development teams, ensuring clarity, alignment, and cohesive execution.

• Partner closely with client-side project managers and technical leads, operating as a trusted extension of the client team.

• Provide mentorship and delivery leadership across technologies including iOS (Swift), Android (Kotlin), React, Node.js, .NET, Python, and cloud-native services.

• Encourage cross-disciplinary collaboration and continuous learning across evolving technical stacks.

Project & Program Delivery

• Own end-to-end delivery of complex, multi-phase programs, ensuring scope, budget, timelines, quality, and operational readiness are consistently met.

• Lead delivery for systems involving:

• AI-powered automation (e.g., voice AI, workflow automation)

• Event-driven architectures

• Mobile and web portals

• Enterprise data integrations (e.g., SAP)

• Manage phased releases, production readiness, and transition into operations and maintenance (O&M) models.

• Define, track, and report delivery KPIs, leveraging data-driven insights to guide decision-making and continuous improvement.

• Apply proactive risk management, especially in environments with compliance, security, and operational reliability requirements.

Client Engagement & Stakeholder Management

• Serve as the primary delivery contact for clients, building trusted, long-term relationships through transparency, consistency, and strategic insight.

• Navigate complex stakeholder landscapes, including unionized workforces and operational teams that may be skeptical of automation.

• Lead executive-level status updates, roadmap discussions, and escalation management.

• Translate complex technical initiatives—such as AI-driven call automation and cloud modernization—into clear business value.

• Travel monthly to client sites to support relationship-building, alignment, and strategic planning.

Technical Oversight & Strategic Enablement

• Partner with architects and technical leads to align delivery execution with AWS-first, cloud-native architectures.

• Oversee delivery of systems leveraging:

• AWS Lambda, API Gateway, DynamoDB (single-table design), Amazon Connect

• Voice AI technologies (e.g., Amazon Nova 2 Sonic)

• WebSocket APIs, AWS Cognito, and event-driven services

• React-based web portals and mobile applications (React Native or native iOS)

• Ensure seamless integration with enterprise systems such as SAP and third-party services (e.g., Twilio).

• Support observability and monitoring strategies using tools such as Langfuse, logging, and metrics frameworks.

• Balance innovation with reliability, security, and compliance requirements.

Process Optimization & Delivery Excellence

• Continuously evolve agile delivery practices (Scrum, SAFe, Kanban) to support distributed teams and enterprise clients.

• Identify and remove delivery bottlenecks using tools such as Jira, Confluence, GitHub, and Azure DevOps.

• Champion automation, CI/CD pipelines, and quality-first engineering practices.

• Foster a culture of transparency, accountability, and continuous improvement across Pods.

Required Skills & Experience

• 12+ years in software delivery, technical program management, or engineering leadership.

• 5+ years managing distributed teams across onshore and offshore locations (Eastern Europe experience preferred).

• Proven success delivering complex, regulated, multi-platform systems in agile environments.

• Strong understanding of:

• Cloud-native architectures (AWS preferred)

• AI-enabled workflows and automation

• Enterprise integrations and data systems

• Hands-on familiarity with delivery tooling including Jira, GitHub, Azure DevOps, CI/CD pipelines, and cloud observability tools.

• Exceptional client-facing communication skills with experience working in high-stakes, compliance-oriented environments.

• Ability to operate consultatively thinking beyond immediate deliverables to long-term client outcomes.

• PMP, Scrum Master, SAFe, or equivalent certifications are strongly preferred.

Personal Attributes

• Client-Centric & Strategic: Builds trust and aligns delivery to real business and operational outcomes.

• Calm Under Pressure: Comfortable leading through ambiguity, scrutiny, and high-impact decision-making.

• Collaborative & Empathetic: Effective working across cultures, time zones, and diverse stakeholder groups.

• Outcome-Oriented: Holds teams accountable while enabling sustainable delivery.

• Consultative Leader: Thinks beyond “what to build” to “why it matters” and “how it lands.”

• Adaptable & Proactive: Anticipates risk, navigates resistance, and leads to change thoughtfully.

Why Join Robots & Pencils?

We blend strategy, design, and engineering to craft technology that transforms businesses and improves human experiences. As a Senior Delivery Manager, you’ll lead high-impact AI and cloud transformation programs, work alongside world-class technologists, and help clients modernize critical systems with confidence, clarity, and care.